The Siege of Ueda Castle (上田城の戦い), also known as the Ueda Conflict (上田合戦) or the Defense of Ueda Castle (上田城攻防戦), were two battles fought between the Tokugawa and Sanada families. On both occasions, the Tokugawa were invading the Sanada family lands during their respective conquests. The first attempt was part of Ieyasu's plans to invade Kai after dealing with the Hōjō. His men fell victim to a deadly water attack, which lead him to eventually call off the siege.

Hidetada lead the second march near Ueda Castle, although his primary objective wasn't taking the castle. His apparent mission was to march along Nakasendō, help the Date and Mogami in the east, and then assist the main forces at Sekigahara. During his march, he intercepted the Sanada troops and was ultimately stalled.

Historically, both battles were won by the Sanada despite their inferior numbers.

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In the first game, both Tokugawa's and Sanada's scenarios, in which the Sanada are lead by Masayuki Sanada and the Tokugawa is lead by Ieyasu Tokugawa.

The Sanada's scenario in Yukimura's upper path story shows Yukimura first told to defeat Tokugawa generals in the north, then lure them into the center into the castle. He is later told to wait for a signal to open the flood gates by his father in order to drown the Tokugawa forces by the rivers and turn the tide of the battle. Frustrated, Ieyasu orders Hanzo Hattori to assassinate Masayuki, where Yukimura must defend him by defeating Hanzo. He then charges Ieyasu's camp and defeats him, winning the battle. However, Yukimura feels that the victory is pointless and begins to lose faith in his resistance against the Tokugawa.

The Tokugawa's scenario in the edit characters' story shows the warrior fight with the Tokugawa against his/her former friend, Yukimura, and the Sanada after the Takeda's defeat at Nagashino. In the battle, the player must succeed in everything that failed in Yukimura's scenario. After winning the battle in the exterior the player must enter the interior of Ueda Castle and proceed to the lowest floor where the player finds Yukimura and Hanzo dueling each other. The player may choose who to defeat, deciding which side the player will fight on in the next scenario, Siege of Osaka Castle.

In Kunoichi's story, Kunoichi must hurry to the bottom floor of Ueda Castle to rescue Yukimura from death by Hanzo. If she saves Yukimura from harm, she will fight alongside him at Osaka Castle. If Yukimura comes to harm, Kunoichi will infiltrate Odawara Castle to prevent Ieyasu from reaching Osaka. Hanzo has a somewhat similar scenario where he infiltrates Ueda to steal a secret letter from the Toyotomi. During this scenario, Hanzo must not be discovered by Sanada troops while trying to reach the bottom floor of the castle in order to retrieve the letter.

In Samurai Warriors 2, The battle remains relatively the same except is more historically accurate. The Tokugawa's scenario is the 1585 battle with the Tokugawa lead by Ieyasu while the Sanada's scenario is the 1600 battle and the Tokugawa is lead by Ieyasu's son, Hidetada Tokugawa.

The Sanada's, a segment of the Western Army, scenario in Yukimura's story has him work with his friends Keiji Maeda and Kanetsugu Naoe. Yukimura starts off by forcing Tokugawa generals towards the river. He then goes to defend the front gate of Ueda. Afterwards, he goes to defend Toishi Castle from his brother, Nobuyuki Sanada, who is fighting in the Tokugawa ranks alongside his wife, Ina. he is then ordered to escort his ally to the flood gates once the Tokugawa forces are in place. Once this succeeds, a frustrated Hidetada orders Hanzo to kill Masayuki. Keiji defends Masayuki while Yukimura defeats the duplicates of Hanzo until he defeats the real one. All forces then charge the main camp and defeat Hidetada. Once victory is achieved, Yukimura and Kanetsugu briefly celebrate when a messenger tells them Mitsunari Ishida and the Western Army were defeated by Ieyasu and the Eastern Army at Sekigahara.

The Tokugawa's scenario has Ieyasu, Tadakatsu, and Hanzo laying siege to Ueda, protected by the combined forces of the Sanada and Uesugi. Yukimura protects the front gate set in hyper mode. in order to weaken Yukimura, the player must overcome ambushes, prevent the flood attack, and avoid Yukimura by going around him and entering the main keep through the back gate and defeat Masayuki. Once done, Yukimura will feel discourage over the loss of the castle and will lose his strength. Kanetsugu, however, will convince the remaining Sanada to charge the main camp. Defeat them to win the battle.

Ueda Castle serves as the battlefield for the scenario in Nobunaga and Nohime's story for the elimination of the Takeda. The Xtreme Legends expansion includes the stage in Katsuie's story. The coalition of the Oda, Tokugawa, and Hōjō battle the combined forces of the Takeda, Sanada, and Uesugi. During the battle, the player must protect various Takeda generals that have betrayed the Takeda. In Nobunaga and Nohime's scenario, sometime in the battle, the Hojo will retreat back to there main stronghold Odawara Castle after news of a siege on it reaches the Hojo, but Kotaro Fuma will comeback later to fight the player. However, playing Katsuie's scenario will have the entire Hojo charge for Nobunaga.

In the first and second game, the battlefield serves for scenario Defense of Numata Castle where Ina protects the castle from Masayuki, and Yukimura. It is also included in the fourth story of Samurai Warriors: Katana where Magoichi and the player come to aid Ina.

In Samurai Warriors 3, the 1600 battle is replaced with Numata Castle and the 1585 battle is the major focus. The main difference is that Ieyasu allies with Ujiyasu, and together they siege the castle. The Sanada army also gains new generals as the Date (Magoichi and Masamune) and the Uesugi (Kanetsugu, Aya and Keiji) forces assist them. A fire attack, ambushes, and other tricks are used to replace the water attack favored in previous titles.

In the first game, the battlefield serves as the first scenario in the Shu Story, where Zuo Ci, Xing Cai, and Yoshihiro rescue Zhao Yun imprisoned in the main keep, telling Zhao Yun that his lord, Liu Bei, was alive, which Zhao Yun thought was dead. After Zuo Ci tells Zhao Yun what to do, he disappears while the other three circle around the battlefield and escape to the southeast, meeting Ginchiyo at Toshi Castle. When news of Zhao Yun's escape reaches Cao Ren, a guardian at the front gate of Ueda, Cao Ren's forces charge toward Zhao Yun, but are stopped by the reappearance of Zuo Ci, giving the other four more time to escape. Once the five warriors reach the southeast after defeating Zhang He, they all set out on a journey to save Liu Bei from Orochi.

The second siege of Ueda Castle is given brief mentions during cinematics before, during, and after Sekigahara in Kessen. If Ieyasu loses Sekigahara, he will be forced to retreat back to his home and reunites with his son for support. Mitsunari and his men follow closely in the rear and call upon their Sanada allies for assistance. While their forces don't clash at the castle itself, Ieyasu's escape path cuts through the open plains of Ueda.